ResourcesBlogTrailblazing Women in Product Management: Sara Edwards, Director of Product at Progressive

Trailblazing Women in Product Management: Sara Edwards, Director of Product at Progressive

Women in Product Management with Sara Edwards

For our next installment of our Women in Product Management Series, I connected with Sara Edwards, Director of Product Management at Progressive Insurance.  

Nicole: Sara, thank you so much for your time to highlight women’s voices in Product Management leadership, and to help us shine a spotlight on women in the career of Product Management. 

Sara: You’re welcome. It’s a pleasure to be here and to be included in this series. 

Nicole: My first question is my favorite because every answer is unique. What led you to Product Management? You have a Fine Arts background, so I know this is going to be an interesting story.  

Sara: I was always a very curious kid. I loved working in groups, exploring, discovering, and experimenting with things, and then sharing with others. I realize now curiosity is a big through line for me. When I went to school, I couldn’t decide if I wanted to be an artist or a scientist. I chose to go to school for design and ended up in a career in tech, which is a beautiful blend of both! I had the great fortune of being a designer at an advertising agency when the iPhone launched. I started my career right as a revolutionary product was sweeping the industry and changing technology and the world as we knew it. Instantly my professional experience used the same approach I did when I was a kid – let’s experiment and figure this out as a group. I started to move into design strategy and helping clients figure this new world out. I kept evolving my career to capture that group exploration and problem-solving approach. 

Later I worked in a technology consulting firm, and that’s where I started to move into Product Management as a career. It was a case of curiosity, timing, and problem solving. When clients were bringing me design problems, I was very curious to understand how they chose it as the right problem to solve. I started working very collaboratively with my clients and business stakeholders and things clicked into place. When I moved to Progressive Insurance, I used that experience to build relationships and conduct workshops with my business partners. I figured out that it wasn’t design strategy that I was doing. I was actually doing Product Management. I was helping find the right problem, define the solution, and because I was a designer, I had the skills to design the solution that we were working on. At Progressive I made the formal change into Product Management, and I’ve been growing that craft ever since. 

You’ve been at Progressive for a while and grown through the ranks of Product Management. It is interesting to see that through line, as you call it, playout in your career. When you’re a kid, you never know what your passions and interests are going to lead to as an adult. What do you love most about Product Management now? 

What I love about design is also what I love about Product Management, which is designing and solving real problems for people. I have a minor in women’s studies, which brings a humanity to my work. I’m always fascinated by people and their relationships to the world, why we do the work, what do people need, what are the systems and context that we need to design for? All those skills and curiosities come together in a really interesting way with Product Management, especially when you add technology as the tool with which you solve those problems. Technology allows you to scale your solutions and drive incredible impact. 

I love the parallel between design and Product Management there. On the flip side, what do you find most challenging about Product Management? 

I think that a strength can also be a weakness depending on how you use it. My biggest strength is that I am incredibly strategic and I’m a visual communicator. The thing I love about Product Management is strategic problem solving and impact. When we’re trying to solve a problem, as a very strategic thinker, I can quickly and clearly see 15 different ways to solve the problem and get it up on a whiteboard. I never think there’s just one right way. It’s about discovering the fastest, most optimal way to get the outcome that you’re looking for. One of the things I find the most challenging is the alignment aspect, helping everybody get on the same page, trying to draw out what really matters to your team and stakeholders who may have different ways of processing information or thinking. Some questions I keep in mind are: Are we talking the same language? Are we using the same terminology? Are we really looking to achieve the same goal or are you trying to accomplish something else? I love it, but it can also very challenging. When I’m struggling to move quickly, I refer to Collaborative Intelligence, my absolute favorite book on working well with people. The answer is always in there. 

It sounds like there has always been a collaboration component that you’ve loved and that continues to play a big part in what you’re doing. Are there any lessons you’ve learned along the way that you’d love to share? 

Yes, for me, relationships are at the core of my approach. Building strong relationships with your team, stakeholders, and executives will maximize your ability to make impact. I firmly believe that. There are 2 components to building good relationships: self-awareness and awareness of others. Anything you can do to increase your self-awareness and gain insight into others will serve you well as a leader and as a partner. I have a personal operating manual exercise I run with my teams to build that awareness right out of the gate. It helps draw out work preferences, values, misconceptions, and strengths. When I say that I like to collaborate and experiment, you probably view that in a very positive light, but tension can arise when people have different approaches and ideas. The operating manual exercise helps get to the heart of who we are and provides insight when a conflict arises. You need to be able to skillfully navigate different perspectives and harness them to make the team stronger. This tool is also a great place to help leaders build relationships in your product orgs. It’s a shortcut to emotional intelligence and an artifact to use when they’re struggling to build consensus. Strong relationships help move through the conflict that is inherent in innovation. 

I would love to tap into that a little more. Do you have some advice on how to strengthen those relationships? Is there something that you found helpful, that you’ve seen make a difference in securing those strong relationships? 

Absolutely, I think curiosity and empathy are key, as well as active listening. That’s at the core of the personal operating manual exercise. As I’ve grown in my career, I’ve learned that the more senior you get, the more you need to listen and the less you need to speak. There’s a lot to learn from somebody when you aren’t seeing eye to eye. Be curious and have empathy for their position. Try to understand where they’re coming from. I talk to my team a lot about understanding the fears and feelings underneath whatever is happening. How does somebody feel about that? Why do they feel that way? What are they afraid of? Why is there resistance? Do they have experience from a previous job that is impacting them now? Try to find out what’s happening there. I apply all the skills we use as Product Managers, like empathy and customer-centricity, to every member of my team to understand what is going on. What is the problem that they’re trying to solve, and how can we work well together so that we’re ultimately all working towards the same goals.  

I love how curiosity has been so integral to your whole development; curiosity for problem solving, for people, for your team, for your colleagues and for executives. That’s really powerful because that’s something most Product Managers can relate to regarding the problems they solve. I like how you encourage them to use curiosity in their relationships as well. Speaking of your team, tell me about what you look for when you are hiring Product Managers.  

This probably won’t surprise you, but I look for intellectual curiosity. I like to hire people who are intellectually curious about whatever it is, not just Product Management. If I asked you to talk to me about bakeries in your neighborhood, or house plants, what would you do? I want to understand how you go about learning something new. It’s very important that Product Managers have an inherent curiosity, follow it, and do self-directed work.  

There are two other things I really look for. One is emotional intelligence. I’ve mentioned that relationships really matter to me, and I want to hire and work with people who have awareness of other people and are thoughtful, sensitive, and caring. I have observed that Product Managers who have those characteristics are very customer-centric, good teammates, and strive to create an environment where everybody thrives.  

The second is excellent communication skills. Product Managers communicate across many levels in an organization and need to be able to flex their message to cater to the needs of the audience. You need a 30-second root cause analysis and recommendation to share with your executives when a release is late, not an in-depth investigation into your backlog. My job as a leader is to help my product people level up and showcase their hard work and impact. Communication is a great place to start. 

I love how you said your job is helping your team level up. They need to have something to work with, and you partner with them to level up their skills. That really affirms that you are investing in them. 

I can’t wait to tap into this next topic because I see so much passion in your Linkedin profile for women, especially women in Product Management. Do you have some advice to share specifically for women who are curious about Product Management as a career? 

One reason I’m passionate about women is my mom is one of seven sisters, and I have two sisters. I was raised in an environment of wonderful, strong, smart women. I’m also a first-generation professional in my family. I’m blazing my own trail, and I love supporting other women as they blaze theirs. As I moved from small consulting firms and small businesses into a Fortune 100 company like Progressive, I met so many people with so many interesting jobs that I had never been exposed to before. I’ve been the beneficiary of a lot of mentorships in my career, because I was curious, and I asked. That’s my advice to women who are looking to change their careers: if you don’t have an example in your organization of what might be next for you, especially in technology, reach outside of your organization and find advocates and supporters to help you blaze that trail for yourself. Women in Product is a great place to find support. 

The other piece of advice for women is to invest in yourself. You are the steward of your career, and you need to invest in where you would like to go. If you need analytical skills, take an analytics class. Invest in your relationships. Find a mentor. Or, if you feel stuck, get a career coach. I started working with Lynne Levy last year after I returned from maternity leave, and it made a huge impact on the quality of my day. You are worth investing in as you choose how to accelerate your career and grow. 

Last question for you, Sara, do you have a motto or a guiding principle that you live by? 

Something I always say to my daughter is, be a little bit more brave than you are afraid. Even if it’s 51% brave and 49% afraid, it’s fine. You just need one extra percent of bravery. Just be you. For as many technology teams as I’ve been a part of, I’ve often been the only or one of a few women. I’ve only worked with a handful of female engineers. There often isn’t a template for women in tech, but I want to live in a world where there is. I want to be that example for other women. I would love to be the example of a woman who is a first-generation professional, who comes from an artsy background, and uses curiosity to build impactful technology solutions, while also being a full-time mom leading an awesome team while working from home. I am proof that all those things are possible. It’s important to figure out what you are looking for and who can help you get there. As a female leader, I’m always available to support anybody along the journey in their career, but I’m enthusiastically here to help women figure out how to create a tech career that feels good to them, especially when they don’t have an example of what that may look like. 

Sara, that sounds very brave. I’m sure many women have already benefitted from your example, and hopefully many more will now as well. Thank you for sharing your story with us! 

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Nicole Tieche
June 16, 2023